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In everyday life, ginger is used in cooking for its hot taste as well as its pungent smell.

Ecologists have studied the relationships of food and culture for many years. During this time, they have found surprising ties between spices that taste good and health-promoting side effects. An example of one of these spices is ginger.

The sensory perception of ginger in the mouth and the nose arises from two distinct groups of chemicals:

The volatile oils, a mixture of terpenoids that give ginger its characteristic aroma and modifies its taste.

The non-volatile pungent chemicals like gingerols, shogaols, paradols and zingerone produce the “hot” taste in the mouth. It is these non-volatile pungent chemicals of ginger that give it, its real value.

Medicine

Ginger for many years has been the traditional remedy for colds. In modern medicine today, zingerone is used to treat a variety of medical problems. Zingerone reacts with free radicals that can cause tissue damage and inflammation. At Case Western University, research has been done showing that a topically applied extract containing zingerone may help prevent some skin cancers. In capsule form, ginger can also be used to replace anti-inflammatory drugs. In a recent study, ginger was found to be more effective than drugs in the treatment of nausea and motion sickness. Zingerone also has a major role in lipid oxidation since it is an anti-oxidant. It weakly inhibits oxidation of phospholipid liposomes in the presence of iron (III) and ascorbate to prevent heart-attacks.

Zingerone used in pharmaceuticals

It is these properties that have made zingerone a molecule of great importance and one that has been produced and synthesized for pharmaceutical use.

Structure

4-(4-hydroxy-3-methoxy-phenyl)-butan-2-one

Chemical Name

Structure of Zingerone

3D Structure of Zingerone

Physical Properties

Synonyms

Zingerone; Vanillyl Acetone

Odour Description

Sweet, Spicy, Ginger, Vanilla, Woody

Appearance

Yellow To Yellow-Brown Crystals

Mol./Wt.

194.2

Formula

Cas. #

122-48-5

Refractive Index

1.54400 – 1.54500 @ 20.00 �C.

Melting Point

40 – 41�C (Solvent – Aq. Ethanol)

Boiling Point

141 �C. @ 0.5 Torr

Boiling Point

290�C. @ 760.00 mmHg

Soluble in

Ethyl Alcohol, 1:1 In 50% Alcohol

Natural Occurrence

Ginger Root; Raspberry; Zingiber Officinale

Nuclear Magnetic Resonance (NMR) Spectrum of Zingerone

Table 1 : H NMR spectral data on Zingerone

Mass Spectrum of Zingerone

Pattern for Mass Fragmentation in the Spectrum

Infrared Spectrum of Zingerone

Table 3 : Infra Red spectral data on Zingerone

NOMURA METHOD

The Bunce & Reeves Method

Historical

Zingerone has been extracted from ginger for the past two thousand years.

A Brief History

Common Name:

Ginger

Latin Name:

Zingiber Officinale

Family:

zingiberaceae

Other Names:

Based on its origin:

African ginger

Black ginger

Chochin (Asian ginger).

Gan Jiang (Jamaican ginger).

The word ginger comes from the ancient Sanskrit ‘singabera’, meaning ‘shaped like a horn’. It first appeared in the writings of Confucius in the 5th century BC. and it has been used medicinally in the West for the past 2000 years. Various virtues have been ascribed to the spice; e.g. Henry VIII recommended it as a pro-phylactic against the plague. It was introduced by the Spaniards to the Americas and is now cultivated extensively in the West Indies. The Portuguese introduced it to West Africa. It is now used all over the world.

Only in the past century has zingerone been produced synthetically. A few interesting and unique syntheses have been chosen. Down the years, the technique of synthesis evolved. Though Lapworth & Wykes were the pioneers in the synthesis of zingerone, their method and reagents were not repeated. Below is a diagram of the apparatus used in their experiment.

Nomura, then Mannich and Merz founded the method used today. This is shown by Kim and Kim’s work. The other interesting method was formed by Bunce and Reeves. This method and the common one used today are elaborated on in the preparation section.

As commented upon in the introduction, zingerone puts the ‘zing’ in ginger. In mustard oil, zingerone uses its properties to give it its flavour.

Zingerone has properties that give its strength of flavour. The higher molecular weight of zingerone in combination with the polar side-chain carbonyl group make zingerone molecules attract each other strongly. As a result, zingerone is not that volatile. The odour of ginger isn’t strong, but the hydrocarbon tail gives it a more intense flavour when it does come into contact with its receptor. Zingerone is also used in artificial flavouring and in fragrances.

A company called “Aroma Fragrance Fine Chemicals” (AFFC) have formulations are used globally for imparting attractive taste and aroma to processed foods and beverages. These chemicals can also add pleasing scents to perfumes, toiletries and detergents. Zingerone is one of their formulations. It is both a flavour and fragrance ingredient. This therefore means that zingerone is important in both processed foods and perfumes.

In industry, zingerone is therefore synthesised using the Kim & Kim’s method for this purpose.

Zingerone contains vanilloid (3-methoxy-4-hydroxy benzene) group in its structure. These phenolic hydroxyl groups provide the possibility to introduce a 4-ether-linked propanolamine side chain. Propanolamine derivatives were obtained by reacting zingerone with epichlorohydrin, and the obtained epoxide compounds were then reacted with isopropylamine, tert-butylamine or guaiacoxyethylamine, respectively, to yield 3 new derivatives shown below.

The syntheses above create third-generation β-adrenoceptor blockers, which possess ancillary cardiovascular actions other than β-adrenoceptor blockade, or cardioselective β-adrenoceptor blockers, have been shown to improve left ventricular function and decrease the risk of chronic heart failure. These β-adrenoceptor blockers are a break through in science and make the synthesis of zingerone very important in industry.

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DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international,
etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules
and implementation them on commercial scale over a 29 year tenure till date Aug 2016, Around 30 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 13 lakh plus views on New Drug Approvals Blog in 212 countries......http://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

The first continuous flow synthesis of C8–C16 alkane fuel precursors from biobased platform molecules is reported. TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) was found to be a recyclable and highly efficient organic base catalyst for the aldol condensation of furfural with carbonyl compounds, and the selectivity of mono- or difuryl product can be easily regulated by adjusting […]

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